Which duo won the first Grammy Award for Best Rap Performance?

DJ Jazzy Jeff & the Fresh Prince won the first Grammy Award for Best Rap Performance.

The Philadelphia duo—DJ Jazzy Jeff, whose real name is Jeffrey Townes, and rapper Will Smith, then known as the Fresh Prince—won at the 31st Grammy Awards in 1989. Their winning recording was “Parents Just Don't Understand,” a comic story about clashes between a teenager and his parents.

The category was new that year, reflecting rap's growing influence in the mainstream recording industry. The award was presented during the non-televised portion of the ceremony because of time constraints. Jeff and Smith boycotted the event, joined by some other rap nominees, because the new category was not included in the broadcast.

Run-DMC, Public Enemy, and Salt-N-Pepa are understandable alternatives because they were central to early hip-hop's rise and received major Grammy recognition. However, none won this inaugural category. The Best Rap Performance award was later divided into solo and duo-or-group categories, then recombined in 2012.